Water → HCID 18507786, compound

HRID 1355672Notes

Reaction equation

HRID 1355672 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6](=O)[C:7](=[O:23])[N:8]2[CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:4][CH:3]=1.O>O.NN>[Br:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7](=[O:23])[N:8]2[CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 18507763HCID 18507763, compound

Product 1

HCID 18507786HCID 18507786, compound

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

6-Bromo-7-methyl-1-naphthalen-2-ylmethyl-1H-indole-2,3-dione (1.04 g, 2.58 mmol) was dissolved in 20 ml of hydrazine hydrate and refluxed for 120 minutes. The reaction mixture was poured into cold water, extracted in ethyl acetate, dried over MgSO4, filtered and concentrated under vacuum to give the crude product. It was chromatographed on flash silica gel eluting with 5% ethyl acetate in hexane to yield the title compound of 2C (0.592 g, 59% yield).

Workup

  1. temperaturerefluxed for 120 minutes
  2. extractionextracted in ethyl acetate
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give the crude product
  7. customIt was chromatographed on flash silica gel eluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8f46fedbdb6744d6bbcc6a0306ac77d0
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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